8 common questions about moving to a new Windows version

In our blog post about Windows 10 End of Life and how it impacts your AVD environments, we discussed the technical aspects of upgrading to Windows 11 and why it’s essential to start the process before Windows 10 reaches its End of Life. However, we didn’t cover a critical aspect of this transition—how to approach the conversation with your customers about making the move.  

Before diving into the technical upgrade, it’s crucial as an MSP to have a strategic discussion with your customers to ensure alignment, address concerns, and set expectations for a smooth transition. Let’s explore some common questions you may get from clients and how to answer them. 

1. “Why can’t we just keep using Windows 10 until it breaks?”

One of the most common objections to upgrading is that some customers believe they can continue using Windows 10 in their AVD environment until it “breaks.” The assumption is that they can ride out the remaining months without facing any immediate consequences. 

Using Windows 10 after its EOL may seem appealing, but the risks are significant. Without official security updates, devices running Windows 10 will become vulnerable to cyberattacks, leaving your virtual desktop infrastructure (VDI) exposed. Compliance regulations, especially for industries that deal with sensitive data, often require up-to-date software and security measures. Failure to upgrade puts your organization at risk for security breaches, compliance violations, and potential financial penalties. 

Additionally, by delaying the upgrade, customers will likely face a longer and more complicated migration down the line, making the eventual transition more painful and costly. 

2. “Isn’t there a way to extend support on what I already have?”

Frequently, customers may wonder if there’s a way to extend support for their existing Windows 10 AVD environment beyond its official End of Life. While Microsoft does offer Extended Security Updates (ESU) for certain editions of Windows 10, this option is generally intended for legacy systems that can’t be upgraded right away. However, it’s important to note that ESU only provides security updates and doesn’t address the broader issues of compatibility, performance, or new feature availability.  

Continuing to rely on outdated infrastructure, even with extended support, creates a temporary solution at best. For long-term success, upgrading to a newer version of Windows—such as Windows 11—is not only a security necessity but also an opportunity to leverage the latest improvements in performance, scalability, and user experience. By upgrading now, you ensure your AVD environment remains secure, compliant, and optimized for future growth. 

3. “Isn’t upgrading just as simple as installing a new update?”

Many customers assume that upgrading to a newer version of Windows in their AVD environment is as simple as installing an update on their devices. They might believe it’s just a matter of flipping a switch or running a quick installer. 

Upgrading a multi-session edition of Windows (such as the versions used in AVD environments) is not currently supported by Microsoft. Attempting to upgrade an old image can lead to unexpected compatibility issues, performance problems, and broken configurations. The upgrade process could be time-consuming and prone to errors, requiring frequent troubleshooting. 

Instead, the best approach is to start fresh by creating a new AVD image with the latest version of Windows. A new image ensures that your environment is secure, optimized, and free from the legacy issues of your current setup. By starting clean, you avoid the risks associated with patching an old, outdated system, and you’ll be ready for the future with minimal disruption. 

4. “We’ve already invested so much in our current setup—isn’t it better to keep it running?”

Another common argument is that customers have already made substantial investments in their existing infrastructure, and they may be hesitant to upgrade if it means significant changes or new costs. They might feel it’s better to stretch the life of their current setup rather than starting from scratch. 

It’s understandable to be concerned about the cost of upgrading, but continuing to rely on outdated systems is a false economy. Legacy systems are often riddled with technical debt—outdated drivers, incompatible software, and security vulnerabilities—that make maintenance difficult and expensive. By upgrading to a newer version of Windows, you’re ensuring that your environment remains secure, compliant, and efficient. 

Additionally, modern Windows editions, such as Windows 11, offer enhanced features that improve performance, scalability, and overall productivity. While there may be an initial investment in building a new AVD image, the long-term benefits far outweigh the costs. In the end, this upgrade will reduce downtime, optimize your environment for the cloud, and provide a more future-proof solution. 

5. “We don’t have time for an overhaul right now—couldn’t we wait until it’s absolutely necessary?”

Some customers might believe that they can delay the upgrade until the last minute, thinking that they have time to make changes closer to the EOL date. They may feel that the process of rebuilding an AVD image is too time-consuming to tackle right now. 

Waiting until the last minute to upgrade is risky and could cause significant disruption. Once an edition of Windows reaches EOL, security vulnerabilities will no longer be patched, and compatibility with newer applications and hardware will decrease. Additionally, last-minute upgrades are often rushed, leaving little time for thorough testing or troubleshooting, which increases the likelihood of performance issues or outages. 

By starting the upgrade process now, you can test and optimize the new environment before the deadline, minimizing disruption and ensuring a smoother transition. Proactive planning gives you the flexibility to resolve any issues well before support ends for Windows 10, ensuring that your environment remains secure, compliant, and high-performing. 

6. “Will the upgrade affect user experience or performance?”

A frequent concern is that upgrading to a new Windows edition might negatively impact the user experience or cause performance issues in the virtual desktop environment. 

Upgrading to the latest version of Windows is actually a chance to improve the user experience. Newer operating systems, such as Windows 11, are designed to be more resource-efficient and optimized for modern hardware and cloud environments. By starting fresh with a new AVD image, you can ensure that the latest features and optimizations are fully integrated into your environment. 

This transition also allows for better scalability, performance improvements, and enhanced security features—ultimately resulting in a more stable, efficient, and responsive virtual desktop experience for end users. 

7. “What if there are compatibility issues with our applications or custom configurations?”

Many businesses worry that upgrading to a newer version of Windows will break their legacy applications or custom configurations, causing operational disruptions. As an MSP, it’s crucial to address these concerns proactively. 

Start by conducting thorough testing to verify application compatibility before rolling out any updates. This helps identify potential issues early and allows you to develop mitigation strategies. When deploying AVD, consider using a clean image to align with modern best practices. This removes outdated or unnecessary software that could introduce compatibility or security risks. 

Additionally, leveraging technologies such as App Attach can help you deliver applications dynamically without installing them directly on the image, reducing complexity and improving flexibility. By planning ahead and using the right tools, you can ensure a smooth, disruption-free transition for your clients. 

8. “What if we ultimately decide not to upgrade?”

As an MSP, it’s important to guide your clients through the potential risks of delayed upgrades. While opting out of an upgrade may seem like an easy way to sidestep short-term disruption, it could ultimately lead to higher support costs and serious security risks. Unsupported systems can quickly become more costly to maintain, with elevated support rates and possibly reduced responsiveness from service providers. In some cases, providers may even discontinue support entirely. 

If your client chooses not to upgrade, their AVD environment will be running on outdated software, leaving them vulnerable to security breaches, compliance failures, and performance issues. As their trusted MSP, you may have no choice but to raise support fees due to the increased complexity of managing outdated systems or even limit the services you can offer.  

Eventually, you may determine that this particular customer is no longer a fit for your company to provide services to them. It’s always best to encourage an upgrade now. This ensures ongoing full support, helps manage costs, and keeps their systems secure and compliant as their business continues to grow. 

Upgrading now saves time and money and reduces risk 

As an MSP, guiding your clients through a Windows version upgrade transition isn’t just about avoiding technical issues—it’s about protecting their business, and yours, from security vulnerabilities, compliance risks, and costly downtime. While some customers may hesitate, it’s your role to provide clear, strategic guidance that makes the upgrade process smooth and cost-effective. 

By addressing concerns early and helping clients plan proactively, you position yourself as a trusted partner, ensuring their environments remain secure, optimized, and future-proof. Don’t wait until they’re facing urgent issues—start the conversation now and help your clients transition before Windows 10 reaches End of Life.

To learn more about Windows 10 EoL and what it means for you, register for our upcoming webinar.